Glycol mono-tertiary-butyl ether compounds are materials that can replace glycol mono-butyl ether compounds, which are components of stripping solutions used to strip resist from a substrate in a process of manufacturing a semiconductor device, a liquid crystal display device, or the like. In addition, glycol mono-tertiary-butyl ether compounds may be used as a high boiling point solvent to provide leveling effects, in fields such as paints, coatings, and the like.
Glycol mono-butyl ether compounds are generally prepared by the reaction of butyl alcohol and ethylene oxide in the presence of sodium ethoxide as a catalyst. However, butyl alcohol and ethylene oxide as raw materials are relatively high in cost, and the catalyst is also expensive, must be used in large amounts, has a risk of explosion, and requires high temperature and high pressure reaction conditions.
Thus, methods of synthesizing glycol mono-tertiary-butyl ether compounds by reacting glycol compounds and butane-based compounds such as isobutene and the like in the presence of acidic catalysts have recently been used. Chinese Patent Application No. 1065656 discloses a method of synthesizing diethylene glycol mono-tertiary-butyl ether by reaction between diethylene glycol and isobutene. However, mixability of ethylene glycol and the butane-based compound in the reaction is so poor that the reaction does not effectively occur. In addition, yield of diethylene glycol di-tertiary-butyl ether as a byproduct is between about 15% and about 30% and thus yield of diethylene glycol mono-tertiary-butyl ether is reduced.